SU507233A3 - Способ получени производных изоиндолина или их солей - Google Patents
Способ получени производных изоиндолина или их солейInfo
- Publication number
- SU507233A3 SU507233A3 SU1893605A SU1893605A SU507233A3 SU 507233 A3 SU507233 A3 SU 507233A3 SU 1893605 A SU1893605 A SU 1893605A SU 1893605 A SU1893605 A SU 1893605A SU 507233 A3 SU507233 A3 SU 507233A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbon atoms
- propoxy
- alkyl
- ethyl acetate
- mixture
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 hydroxy-2-isopropyl-3-propoxy Chemical group 0.000 claims description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052925 anhydrite Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 238000009938 salting Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7209207A FR2175627A1 (en) | 1972-03-16 | 1972-03-16 | Substd 3-(3-amino-2-hydroxypropoxy)-1-isoindolinones - anti-arrhythmi |
| FR7303728A FR2215951B2 (enrdf_load_stackoverflow) | 1972-03-16 | 1973-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU507233A3 true SU507233A3 (ru) | 1976-03-15 |
Family
ID=26216985
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1893605A SU507233A3 (ru) | 1972-03-16 | 1973-03-15 | Способ получени производных изоиндолина или их солей |
| SU2018656A SU496730A3 (ru) | 1972-03-16 | 1974-04-29 | Способ получени производных изоиндолина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2018656A SU496730A3 (ru) | 1972-03-16 | 1974-04-29 | Способ получени производных изоиндолина или их солей |
Country Status (23)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2217000B1 (enrdf_load_stackoverflow) * | 1973-02-08 | 1976-04-09 | Rhone Poulenc Ind | |
| JPS537924A (en) * | 1976-07-08 | 1978-01-24 | Masataka Sumitomo | Plate material for construction |
| JPS5348803U (enrdf_load_stackoverflow) * | 1977-09-30 | 1978-04-25 | ||
| JPS607177Y2 (ja) * | 1978-09-12 | 1985-03-09 | 本州製紙株式会社 | 家具、建材並びにホワイトボ−ド用ボ−ド |
| US4590189A (en) * | 1982-04-02 | 1986-05-20 | Takeda Chemical Industries, Ltd. | Condensed pyrrolinone derivatives, their production and use |
| FR2607506B1 (fr) * | 1986-12-02 | 1989-01-06 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| GB0419481D0 (en) * | 2004-09-02 | 2004-10-06 | Cancer Rec Tech Ltd | Isoindolin-1-one derivatives |
| GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
| GB201517216D0 (en) | 2015-09-29 | 2015-11-11 | Cancer Res Technology Ltd And Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704965D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1308029A (en) * | 1969-07-25 | 1973-02-21 | Sandoz Ltd | Indole derivatives |
-
1973
- 1973-01-01 AR AR247093A patent/AR203991A1/es active
- 1973-01-01 AR AR250934A patent/AR203996A1/es active
- 1973-02-02 FR FR7303728A patent/FR2215951B2/fr not_active Expired
- 1973-03-06 OA OA54846A patent/OA04294A/xx unknown
- 1973-03-08 NL NLAANVRAGE7303291,A patent/NL168510C/xx not_active IP Right Cessation
- 1973-03-13 FI FI756/73A patent/FI55029C/fi active
- 1973-03-14 HU HURO711A patent/HU165990B/hu unknown
- 1973-03-14 US US341307A patent/US3898232A/en not_active Expired - Lifetime
- 1973-03-14 IE IE414/73A patent/IE37405B1/xx unknown
- 1973-03-14 JP JP2909773A patent/JPS5331865B2/ja not_active Expired
- 1973-03-14 GB GB1226773A patent/GB1382770A/en not_active Expired
- 1973-03-15 IL IL41788A patent/IL41788A/xx unknown
- 1973-03-15 NO NO1046/73A patent/NO140348C/no unknown
- 1973-03-15 CH CH378773A patent/CH562791A5/xx not_active IP Right Cessation
- 1973-03-15 CA CA166,339A patent/CA976549A/en not_active Expired
- 1973-03-15 SU SU1893605A patent/SU507233A3/ru active
- 1973-03-15 LU LU67224A patent/LU67224A1/xx unknown
- 1973-03-15 BE BE128837A patent/BE796828A/xx not_active IP Right Cessation
- 1973-03-15 CH CH108075A patent/CH568288A5/xx not_active IP Right Cessation
- 1973-03-15 SE SE7303641A patent/SE385477B/xx unknown
- 1973-03-15 DK DK141473AA patent/DK136360B/da unknown
- 1973-03-16 ES ES412714A patent/ES412714A1/es not_active Expired
- 1973-03-16 AT AT235073A patent/AT322544B/de not_active IP Right Cessation
- 1973-03-16 YU YU711/73A patent/YU35768B/xx unknown
- 1973-03-16 ES ES412715A patent/ES412715A1/es not_active Expired
- 1973-03-16 DE DE2313227A patent/DE2313227C3/de not_active Expired
-
1974
- 1974-04-29 SU SU2018656A patent/SU496730A3/ru active
-
1979
- 1979-08-13 YU YU1969/79A patent/YU35769B/xx unknown
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